Methanol → HCID 70527934, compound

A mixture of 4.524 g (0.028 mole) [2β,2S*,3β)]-3-aminotetrahydro-5-methoxy-methyl-2-furanmethanol, 250 ml methanol, 2.57 g Amberlite CG 120 200-400 mesh (H+ form) and 1.5 g 3A molecular sieves was stirred for 20 hr. then 10 ml triethylamine was added. After 1 hour, the mixture was filtered through diatomaceous earth and filtrate evaporated in vacuo. The reaction was not complete (nmr) so the crude material was stirred with 250 ml methanol and 5.14 g Amberlite CG 120 200-400 mesh (H+ form) for 65 hr., then 15 ml triethylamine added. After stirring for 11/2 hr, the mixture was filtered through diatomaceous earth. The filtercake was stirred 1 hour with 200 ml methanol, 5 ml triethylamine then filtered. The combined filtrates were concentrated in vacuo to give 4.056 g crude product from which 2.189 g methyl 3-amino- 2,3,6-trideoxy-L-arabinohexopyranoside was crystallized from ether as a 2:1 parts by weight mixture (α:β) of anomers as determined by nmr.

1. additionA mixture of 4.524 g (0.028 mole)
2. filtrationthe mixture was filtered through diatomaceous earth and filtrate
3. customevaporated in vacuo
4. addition, then 15 ml triethylamine added
5. stirringAfter stirring for 11/2 hr
6. filtrationthe mixture was filtered through diatomaceous earth
7. stirringThe filtercake was stirred 1 hour with 200 ml methanol, 5 ml triethylamine
8. filtrationthen filtered
9. concentrationThe combined filtrates were concentrated in vacuo

ORD record

ord-29bcb1efa49c4e69af7615083a0f18cf

Source dataset

uspto-grants-1982_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04324726